9. Round 25/09/1999 Middlesbrough FC - Chelsea FC 0:1
10. Round 03/10/1999 Newcastle United - Middlesbrough FC 2:1 yellow card
11. Round 17/10/1999 Middlesbrough FC - West Ham United 2:0
12. Round 24/10/1999 Watford FC - Middlesbrough FC 1:3
13. Round 30/10/1999 Middlesbrough FC - Everton FC 2:1
15. Round 20/11/1999 Arsenal FC - Middlesbrough FC 5:1
17. Round 04/12/1999 Bradford City - Middlesbrough FC 1:1
19. Round 26/12/1999 Sheffield Wednesday - Middlesbrough FC 1:0
22. Round 15/01/2000 Middlesbrough FC - Derby County 1:4 yellow card
23. Round 22/01/2000 Liverpool FC - Middlesbrough FC 0:0
21. Round 29/01/2000 Manchester United - Middlesbrough FC 1:0
24. Round 05/02/2000 Leicester City - Middlesbrough FC 2:1
25. Round 14/02/2000 Middlesbrough FC - Aston Villa 0:4
20. Round 19/02/2000 Middlesbrough FC - Coventry City 2:0
26. Round 26/02/2000 Middlesbrough FC - Leeds United 0:0
27. Round 04/03/2000 Southampton FC - Middlesbrough FC 1:1
28. Round 12/03/2000 Middlesbrough FC - Arsenal FC 2:1
29. Round 18/03/2000 Sunderland AFC - Middlesbrough FC 1:1
30. Round 25/03/2000 Middlesbrough FC - Sheffield Wednesday 1:0
31. Round 03/04/2000 Tottenham Hotspur - Middlesbrough FC 2:3 yellow card
32. Round 10/04/2000 Middlesbrough FC - Manchester United 3:4
33. Round 15/04/2000 Coventry City - Middlesbrough FC 2:1
34. Round 22/04/2000 Chelsea FC - Middlesbrough FC 1:1 yellow card
36. Round 29/04/2000 West Ham United - Middlesbrough FC 0:1 yellow card
35. Round 02/05/2000 Middlesbrough FC - Newcastle United 2:2
37. Round 06/05/2000 Middlesbrough FC - Watford FC 1:1
38. Round 14/05/2000 Everton FC - Middlesbrough FC 0:2 yellow card